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Trifluoroacetic acid → [6-(6-ethoxy-pyridin-3-ylamino)-2-fluoro-pyridin-3-yl]-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 1396169
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HRID 1396169 반응식
C(OC(=O)[N:7]([C:37]1[CH:38]=[N:39][C:40]([O:43][CH2:44][CH3:45])=[CH:41][CH:42]=1)[C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([CH3:25])[CH:23]=3)[N:18]([Si](C(C)C)(C(C)C)C(C)C)[CH:17]=2)=[O:15])=[C:10]([F:36])[N:9]=1)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCCl>[CH2:44]([O:43][C:40]1[N:39]=[CH:38][C:37]([NH:7][C:8]2[N:9]=[C:10]([F:36])[C:11]([C:14]([C:16]3[C:24]4[C:19](=[N:20][CH:21]=[C:22]([CH3:25])[CH:23]=4)[NH:18][CH:17]=3)=[O:15])=[CH:12][CH:13]=2)=[CH:42][CH:41]=1)[CH3:45]
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참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 58485918(6-ethoxy-pyridin-3-yl)-[6-fluoro-5-(5-methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

생성물 1

HCID 67442878[6-(6-ethoxy-pyridin-3-ylamino)-2-fluoro-pyridin-3-yl]-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone수율 50.2%

시약·촉매·용매 1

HCID 11
1,2-Dichloroethane
용매

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온도
80 °C

실험 절차

To (6-ethoxy-pyridin-3-yl)-[6-fluoro-5-(5-methyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (71, 0.200 g, 0.309 mmol) in 10 mL of 1,2-dichloroethane, trifluoroacetic acid (0.80 mL, 10.0 mmol) is added. The reaction is stirred at 80° C. for 2 hours, then poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with 2-15% methanol in dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (P-3045, 60.7 mg). MS (ESI) [M+H+]+=391.9.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material is purified by silica gel column chromatography
  6. washeluting with 2-15% methanol in dichloromethane
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-86896253138c4010bfce734b454bab4e
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08901118B2

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